It's Complicated
by mymindpalace
Summary: Dean/Sara SPN/FWB Sara couldn't live in Chicago anymore, not with everything that had happened there. A fresh start in Colorado is what she needs. And that just happens to be where Dean and Sam have a new case; what will happen when the pair cross paths


_Well here it is, my first Dean/Sara story. _  
><em>I choose to set the story after the end of season 2 of Supernatural, so for the purpose of this fic Dean has only one year left to live.<em>  
><em>While this story is DeanSara centric I am also attempting to have a somewhat Supernatural plot in here, lol_

_Anyway, please enjoy the story and let me know what you think._  
><em>Sara<em>  
><em>xx<em>

* * *

><p><strong><em>Chicago, Illinois <em>**

Sara lifted up the last box and carried it out into the hallway, putting it down with the others that the removal men where bringing down to the van that she had hired. Walking inside the apartment she pulled out her key and set it on the kitchen counter. This was the last time she was going to be inside this apartment, the last time she was in this city.

She felt a lump in her throat but knew that she had to do this – she couldn't continue living here with all of the memories of what happened with Ben and Riley. She had thought she could move on and forget about it – Ben and her weren't ever a proper couple but she had thought that things could have gotten serious between them if they wanted to put the work in and try. She supposed they were just too different – she wanted to find Mr Right and he just wanted Miss Right Now. A few weeks after walking in on Ben and Riley in bed together she had decided that she needed a fresh start. Somewhere no one knew her or her past, where she could help people without feeling judged. It was hard breaking the news to her group of friends, she would be a liar if she said she didn't find it the hardest thing she had done in a long time. But it also left her feeling good – there was a sense of adventure of leaving behind the city that had been her home since she started med-school and travelling to a new town where she would make new friends – and even possibly find The One. Sara laughed aloud at the last thought. Her love life didn't have the best track record as of late so for now she was going to focus on herself and her new job and let fate work its magic.

"Well, looks like this is goodbye" Sara muttered to the almost empty apartment. Although Riley had moved in with her most of the furniture and decorative items belonged to Sara. She was taking the paintings and knick-knack with her but the sofa and dining table were staying as well as the bed in her old room.

Walking to the door she took one last look at the apartment before locking it behind her. She had left a small note under the key on the counter reminding Riley that the security code needed to be changed but apart from that she left no other message. It wasn't that she didn't want to speak to Riley or the others but that it was easier this way – for her and them; a clean cut. Lifting up one of the boxes she made her way to the elevator to finish packing on the van and starting the long drive to her new home.

* * *

><p><strong><em>Sioux Falls, South Dakota<em>**

Dean pushed open the motel door, arms filled with bags of food and a six-pack of beer. It had been a few weeks since they had killed yellow eyes and Dean had confessed to selling his soul for Sam's life and a year to live. They hadn't talked about the deal much. Not because Sam didn't want to; the kid was like a dog with a bone, staring at Dean with concerned eyes when he thought Dean couldn't see him. No, they hadn't talked about it because Dean knew that Sam would want to find a way to get out of this deal and there was no way that was going to happen. Weltch out of the deal and Sam goes back to being nothing more than a rotting body in the soil.

"Honey, I'm home" Dean laughed as he kicked the door shut behind him, tossing the motel room key onto a table that sat near the door, before setting the bag that smelt of greasy burgers and fries down on the small kitchenette counter, along with the six pack of beer.

"I'll be out in a minute" Sam shout was muffled from behind the cheap wooden bathroom door. He was taking a quick shower to wash off the remains of the hunt that they had just finished – a salt and burn that was pretty standard yet also pretty dirty.

Taking off his jacket and throwing it onto his bed Dean grabbed a beer and a burger before dropping down onto one of the chairs at the small table in the centre of the room. Taking a large bite of the burger, ketchup dripping onto his fingers, Dean started flicking through the newspaper that Sam had bought on the way back from the cemetery.

Scanning over the articles and looking for anything suspicious Dean paused as he found something that might be right up their street. Down in Glenwood Springs, Colorado a man had been found dead in an elevator in Hotel Colorado, after suffering a major heart-attack. Normally something like this would just be skimmed over by Dean – people died natural deaths every day. But the fact that this accident happened in a known haunted hotel made Dean perk up. It could end up being nothing but Dean wouldn't feel comfortable until they at least checked the place out.

"Looks like I found us our next case" Dean said around another mouthful of burger as Sam came out of the bathroom, towelling his hair, drops of water falling onto his grey t-shirt and appearing almost black.

"Yeah – what is it?" Sam questioned, digging around in the bag that Dean had brought back with him and scowling at the greasy item of food; next time he was picking up dinner – preferably something that wasn't soaking in grease.

"A haunted hotel" Dean grinned over the rim of his beer bottle, "Hotel Colorado, guy goes into the elevator on the 5th floor, winds up dead by the time it's on the 1st from a heart attack" Dean explained, smiling at the prospect of finding an honest to God haunted hotel, "which of course wouldn't be weird on its own but for ten points Sammy guess which hotel has reports of haunted rooms and a haunted elevator?" Dean was practically grinning like the cat that caught the canary by now.

"Calm down there, kiddo" Sam said, jokingly, as he sat down opposite Dean and ate his own burger, albeit with less gusto than his brother.

"Come on Sam, tell me you don't get excited at the thought of haunted a ghost in an actual haunted hotel?" Dean's grin was ear splitting now, at the possibility of, not only working a case in a hotel that was haunted and not just all media hype to get in the customers, but one as famous as Hotel Colorado.

Turning the newspaper around to get a better look at the article, which was printed underneath a picture of the grand Hotel Colorado, Sam nodded his head. Dean was right, this did sound like their kinda gig. Having a heart attack and dying could happen to anyone. But having a heart attack and dying in a known haunted hotel? Not so much.

"You're right, we should probably check it out" Sam said, trying not to laugh at the way Dean took a large gulp of his beer before getting to his feet.

"Well Colorado is about ten hour's drive from here so we should hit the road a.s.a.p." Dean was already grabbing items that he had left around the motel room; over-shirt, gun clip and a few other bits and pieces that he shoved into his duffel.

"Come on Samantha, time to hit the road" Dean teased Sam as he grabbed the keys to the Impala and started loading the trunk up for their journey.

* * *

><p><strong><em>Glenwood Springs, Colorado <em>**

Sara climbed out of the truck, a weary smile on her face. She had left Chicago early in the morning to get a flight down to Colorado and then a few hours' drive from the airport to her new apartment building; it was now night time and the sky was dancing with stars, the moon bold in the sky. To say she was tired and stressed would be understating it. At the airport she had been flustered, trying to make sure that all of her luggage and belongings had made it from Chicago with her – she may not have taken that much but what she did take meant a lot to her.

Climbing out of the truck she wrapped her coat tightly around herself. She was only wearing an old pair of jeans and t-shirt because she knew that she would be moving boxes around but now she wished she had put something warmer on; Chicago may be the windy city but Colorado was doing its best to beat it in the ice cold wind that was traveling up the street as the early December chill caused goose bumps to rise on her skin.

"Thanks guys" Sara said to the removal men that were already lifted boxes and various items of furniture from the back of the van, ready to take it upstairs. Walking ahead, a box labelled 'Kitchen' in her arms she hit the elevator for 'Up'. After waiting a few moments she climbed inside and rode up to the third floor. Sara walked down the carpeted wide hallway, with decorative plant pots on the floor and contemporary paintings along the walls until she reached a door with gold plated numbers announcing that it was apartment 62a. Pulling out a freshly cut key she opened the door, the moon shining in throw the large windows, casting shadows in the corners.

The apartment was smaller than the one she had in Chicago, yet at the same time it felt more spacious. With hardwood floors and cream walls it was a blank canvas that she could easily put her personality into. The centre of the room was open, with a counter separating the kitchen area from the living area. An oak door led to a small hallway that contained three more doors; one led to a small bathroom, and the other to the bedrooms – the master bedroom was located at the end of the hallway.

"Just set the boxes over there, thanks," Sara said with a smile to the removal men that had followed her up.

It took roughly about forty-five minutes to get all the boxes and pieces of furniture moved from the van into her new apartment and by then all Sara wanted to do was crack open a bottle of wine and sit down on her couch. The couch she currently did not own.

Walking into her bedroom she threw herself down on the large mattress, bouncing slightly before settling in the middle, arms and legs akimbo in her exhaustion. Laying there for a second, just letting everything wash over her before she pushed herself upright.

"OK, I need to get this sorted" She said aloud to herself, pushing herself to her feet and walking out into the main area of the apartment. Pilled in the centre of the room was dozens of boxes, all neatly labelled and taped shut.

"Ok, where to start…" She asked herself as surveyed the heap of boxes, trying to determine the best way to do this. It was late at night so she knew that there was so way she was going to get everything organized tonight, so she came to the conclusion that getting the bedroom and important items for the bathroom and kitchen that she would need in the morning would be priority. Pulling her curled hair back into a loose bun she made a start on what was going to be a long night.

****X X X****

Just over two hours later and, while the apartment was nowhere near ready, it would do for now. In the bedroom she had the bed sheets all made up so that, while she had yet to purchase an actual bed, she could sleep comfortably tonight. A lamp and some books were also unpacked as well as essential toiletries like shampoo and toothpaste. A few pots and pans had been taken from their box but Sara surmised that she would probably just take the short walk into town and but breakfast.

Walking from the bedroom with an empty box she set it aside, thinking that she could find out where she could bring them to recycle them when she was done unpacking. Rubbing a weary hand over her face she made quick work of taking a shower to get rid of the dusty grime that covered her before slipping into a pair of shorts and tee.

Letting herself fall less than gracefully onto her mattress she pulled the covers around herself before drifting off into an exhausted sleep. It was nearly 2.00am and she had to get up early tomorrow to finish unpacking the rest of her stuff and to go and meet her new boss at the medical clinic in the afternoon.

* * *

><p>The rumble of the Impala's throaty engine could be heard almost a minute before she was seen. Dean steered the classic cars' large body around the tight corners and past other parked vehicles to an empty parking space at the end of the gravel drive outside Hotel Colorado, only his many years driving the car allowing him to get the muscle car into the parking space in one swift motion before cutting the engine.<p>

"Rise and shine Sammy" slapping Sam on the chest Dean woke him from a somewhat peaceful slumber, laughing as Sam jumped upright in the seat, hair sitting at odd angles on his head.

"You're such a jerk" Sam grouched, attempting to make himself look somewhat awake as he pulled his hands down his face, scanning the scenery around them. The parking lot of the hotel, while not completely full, was still substantially packed considering the events that had recently taken place.

"Guess a little death isn't enough to put some people off staying here," quipped Dean as he glanced around at the number of cars with a raised eyebrow before pushing himself from the relatively warm Impala into the harsh winter night.

Grabbing their bags from the trunk they made their way towards the entrance, pushing past each other to try and be the first inside the warm confines of the building. Walking across the wooden floors, their heavy boots echoing around the hallway they sidled up to the check in desk.

"Welcome to Hotel Colorado, can I help you?" tall-blonde said with a smile that was aimed more at Dean than Sam.

"Yes you can," Dean said suggestively, grin growing bigger as he saw the tall-blondes whose name tag read 'Terri' blush slightly, "Me and my brother have a reservation; it should be under Young"

Terri nodded her head with another smile towards Dean, almost completely ignoring Sam's existence completely as she leaned forward, her ample cleavage straining against her white silk blouse as she pushed the sign-in book towards Dean. Picking up the pen Dean quickly signed his John Hancock, giving Terri a wink.

"Here's your room key Mr Young" the gold key with classic round keychain with the room number in large font slide across the desk to Dean. As he picked up the key he noticed a papery feeling underneath, grinning as he realised that Terri had quickly scribbled down her phone number.

"What's that?" Sam questioned, trying to see the piece of paper that Dean held in his hand as they grabbed their bags and made their way towards the elevator to make their way up to their room on the fifth floor.

"Nothin'" Dean said as he shoved the paper into his pocket as they got into the empty elevator, Sam pressing the 'Close Doors' button so that no one else could get on with them. As soon as the doors were closed Dean pulled the EMF meter from his pocket and held it up, watching to see if anything was being picked up as they travelled from the ground floor up to the fifth floor of the hotel.

"Anything?" Sam asked, eyes scanning the compartment looking for any signs of supernatural activity that would give them some clues as to what had happened here.

"Bub-kiss" Frustrated Dean turned off the EMF and put it into his pocket just as the elevator stopped at their floor, "After you Samantha" jibbed Dean with a snort, Sam shaking his head as he walked out into the darkened hallway, Dean not far behind.

"What's the room number again?" Sam questioned as he hitched his bag higher on his shoulder.

"Room 325" Dean said, pointing to their room which was at the end of the corridor. Dean quickly opened the door and flicked on the light, the ornate lampshade ruining the efforts the light bulb was trying to make by dulling the glow to a dim version of the harsh lampshade-less motel rooms that the Winchester's usually stayed. Although while the hotel was far classier than any motel they had ever stayed in as children or young adults the furnishings were antique enough that they didn't feel too out of place; there was an air of history to the old building – one that Sam and Dean were going to be digging very deep into over the next few days.

Throwing his duffle at the end of the bed nearest of the door Dean pulled off his jacket before falling onto the bed, hands laced behind his head.

"Better catch some 'Z's' Sammy, we got a big day tomorrow"

****X X X****

The next morning Dean woke up at just after 6.30am. Growing up with a military man for a father meant that some things rubbed off; how to handle a gun, hand to hand combat and apparently the annoying habit of waking up at 6.30am not matter how late he got to sleep the previous night.

Quietly getting out of bed Dean made his way across the room, past Sam who was still sleeping soundly for once. Ever since Dean made his deal and sold his soul it seemed like neither one of them got a good night's rest, the worry that was troubling them and eating away at the back of their minds in the light of day came to the forefront of their minds as they slept and devoured their dreams.

Grabbing a clean t-shirt and jeans Dean made quick work of showering and brushing his teeth. He had a growth of stubble on his chin, more than he usually did but he was too hungry and in need to caffeine to bother shaving and besides, chicks digged the lumber-jack look.

Scribbling a note of the hotel stationary Dean let Sam know that he was going out to grab breakfast and would be back later _bitch. _

_****X X X****  
><em>

Walking down the almost empty street Dean stuck his hands deep into his black cargo jacket pockets. It was nearly 7.00am in the morning but the winter air was frigid, sky still dark. Just down the street he spied a small café that was just opening, the smell of fresh coffee wafting down the street and making him take his steps a little faster.

* * *

><p>Sara rolled over, the duvet falling off her shoulder making her shiver. Rubbing her eyes she looked at the room around her, still partially covered in unpacked boxes. She smiled as the warm buzz of excitement and anticipation fluttered in her stomach at the thought of this new adventure that she had just started.<p>

Climbing out of bed she quickly grabbed a warm shower and debated for approximately ten minutes over what she was going to wear for the day. She was going to the clinic, her new job, in the afternoon and probably wouldn't have time to change after the errands that she was going to run this morning. She finally decided on a pair of brown skinny jeans and a smart mustard coloured top – formal casual was the best option in these situations. After drying her hair she slipped on her nude pumps and was out the door before 7.00am – life as an intern had programmed her body clock to rise early and sleep when she could – a trait that she could try and forget now that she was going to be working a nine-to-five job.

****X X X****

Pulling her tan jacket tightly around herself, her wavy hair blowing back and forth in front of her eyes she made her way towards the little café she had spotted when she had arrived in town last night – the sign promising a hearty early bird breakfast was one that had her mouth-watering as she stepped inside the door, a small antique bell signalling her arrival.

A small smile graced her lips at the smell of fresh coffee and baked goods. Big city café's never had the atmosphere that small town café's like this one did; the homely feel that no matter what time you came in you were always welcome with a warm cup of coffee and a slice of pie.

As it was early there was only a few other people in the café with her; an elderly man that was sitting at the counter, his arthritic hands already wrapped around a mug of coffee, a woman in her mid-forties that looked like she had been up all night, her hair unruly and make-up smudged under her tired eyes.

Walking over to the counter Sara sat down and waited for the waitress to finish with her customer. Pulling out her cell she checked to see if she had any new messages, turning around at the sound of the door opening, the bell signalling the arrival of a new customer.

A tall man with short hair and a slight growth of stubble walked in, _well that's more of a swagger, look at the way those hips move; _Sara thought, her cheeks blushing slightly as the thought made its way across her mind before she watched from the corner of her eye as the stranger took the seat one down from where she was sitting.

"What can I get for ya sweetie?" the waitress said, a smile on her face despite the fact that she looked like she would much rather be at home, under her warm duvet.

"Eggs and toast with some coffee, please" She asked with a smile, the waitress scribbling down her order before passing it through to the kitchen.

"And what about you, son?"

"Just a black coffee thanks" Dean said, lifting yesterday's newspaper that was sitting on the counter and scanning through it for any updates on their case. He smiled up at the waitress as she set the steaming black cup of coffee in front of him, taking a large gulp mindless of the steam rising from the mug.

"Excuse me" Dean looked up from what he was reading at the sound of a female voice close to him. He was pleasantly surprised to see that the voice belonged to the attractive brunette that he had spotted when he walked in.

"Could you pass me the sugar, this one seems to be empty" she laughed, holding up said sugar-container.

"Sure, no problem" Dean said, passing it over, fingers brushing against eachother. Dean smirked to himself as he saw her blush as she took the sugar from him before pouring it into her own cup of coffee before handing it back.

"Thanks…" She left the end of the sentence hanging.

"Dean" he introduced himself with his patented Dean Winchester "Ain't I Adorable and Sexy at the Same Time" smile.

"Sara" She placed her smaller hand in his, grinning back at him. God he was gorgeous; with large green eyes and a dazzling smile he had her in a tizzy – just because she had told herself before she got to this town that she wasn't getting into a relationship didn't mean she couldn't have a little flirtatious fun. And he looked like the kind of guy that enjoyed this kind of fun.

"So do you live here or are you just passing through" Sara asked, taking a sip of her coffee, defiantly not bating her eyelashes as she spoke. _Nope, defiantly not_.

"Just passing through – me and my brother," Dean wasn't sure why he added the last part. Probably because for some reason everyone assumed him and his brother were gay and he did not want to give Sara that impression. Nope, he was _definitely_ batting for her team.

"That's nice – I'm just new to town myself – moved from Chicago just yesterday" Sara continued, "It's definitely a change" the laugh was half amusement half nervous at the unknown that lay ahead.

****X X X****

The pair continued their flirtations for another half an hour, coffee cups refilled and gone cold twice before leaving to go their separate ways; not before Dean made a suggestive "Maybe I'll see you around sometime", returned by Sara quickly scribbling her cell number on a napkin.

Dean had made sure to grab a coffee to go before leaving or else Sam was going to be in a pissy mood when he got back – Kid did always get cranky when he didn't have his morning caffeine fix.

"Where the Hell have you been!" was practically shouted at him as he opened the hotel room door. _One cranky brother – check._ Walking into the room, a half-smirk on his face set the cup of the small desk in the room before walking over to the bedside table and lifting up the piece of paper that he had used that morning.

"I left a note" as if that should explain everything.

"I had no idea where you were or what had happened – I was going out of my mind here!"

"Come on Sam, it's not that big a deal Sam…" As soon as he spoke the words the realisation of why Sam was freaking out dawned on him. The deal. One year left to live and Sam probably thought that Dean had upped and left him or been dragged away by the hellhounds while he was sleeping.

Clearing his throat; almost awkwardly, Dean lifted up the cup of coffee and handed it to Sam, "So what's the plan for today". It was his way of apologising without actually saying the words – letting Sam decided their next move, how they were going to move forward.

"Well we need to research as much about this hotel as possible; check out any strange deaths and see if they fit the M.O. of this guy in the elevators death" arms crossed in front of his chest Sam was in his element.

"Aye aye, captain" Dean joked with a mock salute, smiling when Sam shook his head in amusement, a smile gracing his own lips.

****X X X****

Sara couldn't stop the small smile from staying on her lips all day; Dean had put her in such a good mood, made her feel happy for the first time in a while. Walking into what was going to be her new place of work; the clinic in town, she had a spring in her step.

"Good morning, I'm supposed to be starting here tomorrow, I'm Sara Maxwell" Sara greeted the receptionist, a petite woman with her hair in a bun, dark blue eyes hidden behind the heavy frame of her black rimmed glasses.

"Dr. Maxwell, so nice to finally meet you! I'm Linda" she bounced up from her chair behind the counter and came around to shake Sara's hand, "I'll bring you to meet Dr. Naylor – he's the best doctor we've ever had"

Walking down the short corridor to the exam rooms and office's (Sara noted that her name had already been stencilled onto her) before coming to the office at the end of the hallway with the words "Dr Patrick Naylor, Head Physician".

Linda knocked on the door and only had to wait a few moments before a gruff sounding voice called for them to come inside. The office was large, an oak desk in the centre of the room with several filing cabinets, some overflowing, scattered about the room.

"Ahhh, Miss Maxwell, so nice to finally meet you" his smile was warm as he held her hand in both of his. Although he had sounded quite gruff through the door his appearance was anything but. With white hair perfectly combed and a fluffy white beard he could be mistaken for Kris Kringle himself.

"Come right this way and I'll show you around the place"

****X X X****

After taking the grand tour and getting acquainted with the other members of staff; Linda on reception and the three nurses that worked at the clinic Sara was on her way home. Getting out of the cab; because no way was she walking home in these high heels in the cold; she was puzzled by the trucks that were parked outside. Was someone else moving into a new apartment? But then why did it seem like a lot of people were leaving?

"Excuse me, could you tell me what's going on?" She asked one of the passer's by, a man she had recognised going into an apartment down the hallway from her yesterday when she was moving in.

"Termites – they're evacuating the whole building, putting us up in the Hotel Colorado"

Staring at the building in shock Sara could feel her previously good mood beginning to vanish. This was so not what she needed right now.

**X X X  
><strong>

Walking into the hotel Sara huffed as she hiked her bag higher on her shoulder, pulling another suitcase behind her. She was going to have arms like Madonna after lugging all of this around. She couldn't believe her luck – trust her to move into the only apartment building that would be infested with termites.

After checking in she made her way to the elevator and squeezed inside – trying to fit herself, luggage and two other passengers was a tight fit – she was almost panting from trying to stay upright as she travelled up to the fifth floor. As soon as the doors opened she was out, relieved at being able to move her arms properly again.

**X X X  
><strong>

Once Sam and Dean had made it back from the library they were both exhausted and hungry. Turns out a hotel like this had a lot more deaths than you would think – they had spent the entire afternoon going through old newspaper articles and obituary's to try and determine which could fit the circumstances of their dead guy.

They had narrowed it down to two possible suspects; one was a man, David Bell in 1891 who was working at the construction site and died by falling down what was now the elevator shaft and breaking his neck. Another was a little Victorian girl, ten years old, that was staying with her family over the Christmas period when she had fallen ill and died – there had been several sightings of her in the hotel although Sam and Dean had yet to find anything. Both cases would have reason to be causing these accidents and deaths but they would need to do more research before they could be sure.

"I'm gonna grab dinner" Dean announced as he lifted his jacket from where it was thrown at the end of his bed. Sam nodded his head absentmindedly as he scanned the print outs he had made from the library, looking for any clues as to who their ghost was hidden in the lines on the page.

Shaking his head in amusement at his geeky brother Dean stepped into the hallway just as the elevator doors at the other end opened. A surprised smile sprung onto his lips when he saw the woman, Sara, step out arms laden in luggage.

"Let me help you" he said as he made his way to her side and grabbed her falling bag, lifting it with ease.

"Dean!" She exclaimed in shocked surprise to see him; in all the chaos of trying not to fall under the weight of her things she hadn't seen him approaching until he was by her side.

"The one and only," he joked, walking with her down the hall as she headed towards her room, "so what are you doing at the hotel – I thought you had an apartment?" he laughed when he saw the exasperated expression on her face, grinning as she looked up at him at his laugh, a smile gracing her own pouty lips.

"Turns out my bad luck followed me from Chicago and I managed to move into a termite city"

"Well maybe you're lucks about to change," Dean drawled suggestively as they stopped in front of her hotel room door, "Come out to dinner with me"

Dean usually didn't ask girls out to dinner – usually he was already out in a bar with a shot or two in his belly and someone would catch his fancy; a few compliments and smiles and he wouldn't be going home alone. But for some reason he wanted to take Sara out to dinner and make her crappy day a little less crappy – and hey, if one thing led to another he wasn't going to complain.

"Sure, I'd like that" She replied with a smile, a slight blush on her cheeks. Maybe her luck wasn't all bad after all.

* * *

><p>Well, there is chapter one!<br>Please leave a review and let me know what you think ;)


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